Azo dyestuffs of the 2-hydroxynaphthalene-3-carboxylic acid arylamide series



Patented Jan. '15, 1929.

UNITED STATES PATENT OFFICE.

mm'n WAGNER, or SODEN-N-THE-TAUNUS,.AND o'rro sonsr, or BIGGEST-ON- mnn-mm, GERMANY, ASSIGNORS 'ro GRASSELLI DYESTUFF conroaa'rron, or NEW YORK, 1v. 2, a conrona'rron or DELAWARE.

AZO DYEB'IUFI'S OF THE B-HYDROXYNAPHTHALENE-3-GARBOXYLIC ACID ARYL- AMIDE SERIES.

.Ilo Drawlngn Application filed July 8, 1928, Serial No. 120,522,

The present invention relates to the new azo dyestufis of the general formula:

o-a m if." i ll.

A-z 0. l. wherein Z represents alkyl or aralkyl and R represents an aryl radicle and causing the diazo compound thus obtained to act upon a 2-h droxy naphthalene 3 carboxylic acid ary amide. The aromatic amines to be used in this rocess as starting materials may be obtained for instance, by causing an aryl sulfochloride to act upon a 4-amino-2-m'tro-1- alkoxy benzene and subsequently alkylating or benzylating and reducing the resulting com ound. T e dyestuffs in uestion can be produced in substance, on a su stratum or on the fibre. They are like the dyestuffs described in our 0 prior application soluble in concentrated sulfuric acid with a bluish-violet color.

and in Germany .Iuly 25, 1828.

The following examples serve to illustrate our invention but are not intended to limit it thereto:

1. 10 parts by weight of 4-benzenesulfo- 4| methylamino-2-amino-1-methoxybenzene are suspended in 100 arts of water with addition of 11 parts 0% hydrochloric acid of 20 B. and 200 parts of ice. diazotized with a solution of 2,4 parts of so dium nitrite in 15 parts of water .and the diazo compound is then coupled with a solution of 11 parts of 2.3-hydr0xynaphthoic acid 5-chlor-2-toluidide in 400 parts of water and 10 parts of caustic soda solution of B. Thus a claret-red precipitate is produced which may be filtered off, washed and dried.

The resulting dyestufl' is soluble in sulfuric acid of 66 B. with a bluish-violet color. .It has the probable formula:

The mass is then OCH:

H 7 OH: N-OH: (Um-NO-cl 0: ii i 2. For dyeings on yarn there is used a bottoming bath prepared with:

11,85 grams of 2.3-hydroxynaphthoic acid- 5-ch10r-2-toluidide, 30 cc. of caustic soda solution 34 1%., 40 cc. of sodium Turkey-red oil, 50% strength, 500 cc. of hot water, the whole made up with cold water to one litre.

A diazotizing bath prepared as follows:

5,84 grams of 4-benzenesulfomethylamino- 2-amino-1-methoxybenzene are dissolved in 50 cc. of hot water and 5,2 cc. of hydrochloric 1,eee,eee

yarn -a bright claret-red tint. with a red hue acid of 22 B.; the solution is cooled with of good fastness. 50 grams of ice and then mlxed w1th a'solut1on Similar dyestuffs are obtamed if instead of of 1,44 grams of SOdllllIl n1tr1te in 10 cc. of the components specified 1n the foregoing ex 5 water. The whole 1s then made up w1th cold amples there are used, on the one hand, other water to one htre and before bemg used there 2 hydroxynaphthalene 3'- carboxyhc acid are added 4 arms of SOdlllIII acetate arylam-ldes and, on the other hand, other 4- The cotton yarn, after being bolled and arylsulfone-alkylammo-Z-ammol-alkyloxydried, 1s well impregnated w1th the bottombenzenes.

10 ing-bath, wound ofi and then dyed 1n the d1- In the following table are stated the azotlzmg-bath, whereupon 1t 1s wound ofl', shades obtamable by some other dyestuffs well washed and soaped whlle b'olhng. falhng within the scope of our present inven- In th1s manner there is produced on the t1on:

I Diazotizing Coupling components. Shade.

I No. 1 4-benzenesullonmethylamino-2-amino-1-meth- I 2 hydroxynaphthalene 3 carboxylic acid-o Reddish-Bordeaux.

oxy-benzene. toluidide. No. 2 4 ehlorobenzeneeulfonmethylamino 2 amino 2 hydroxynaphthalene 3 carboxylic acid o Very bluish-red. l-rnethoxy-benzene. toluidide.

N 0. 3 4- chlorobenzenesulfonmethylemino 2 amino 2 -hydroxynaththa1ene 3 carboxylic acida Bluish-red.

l-methoxy-benzene. naphthyiamide. N o. 4 4-naphthalene -fi-sulfonmethylamino-2 -emino- 2 hydroxynaphthalene 3 cerboxylic acid 5 Reddish-Bordeeux.

l-methoxy-benzene. ehloro-2-toiuidide. No. 5 4-naphthalene-,9-su1fonmethylamino-2-aniino- 2-hydroxynaphthalene-3-carboxylic acid-4- Yellowish Bordeaux.

l-methoxy-benzene. chloro-Z-amsidide. No.6 4-naphthalene-B-sulfonmethylamino-2-emino 2 hydroxynephthalene 3 carboxylic acid a Bordeaux.

l-methoxy-benzene. naphthylemide. No. 7 4-naphthelene-fl-sulionrnethylamino-Z-amino- 2 hdroxynaphthalene 3 carboxylic acid fl Bordeaux.

l-methoxy-benzene. naphthylamide. No. 8 4-nnphthalene-a-sulfonmethylamino-2-amino- 2 hydroxynaphthalene 3 cerboxylic acid 4 Yellowish Bordeaux.

. l-methoxy-benzene. chloro-2-anisidide. No. 9 4-naphthalenew sulfonmethylamino- 2- amino 2 hy r xylmp fl fl 3 y 801d B e Wi h B rdea xl-metho'xy-benzene. naphthylamide. No. 10 4-toluene sulfonmethylamino-z-amino-l-meth- 2 hydroxynaphthalene 3 carboxylic acid o Very bluish red.

oxy-benzene. toluidide. No. 11 4-toluene su1Ionmethy1amino-2-amino-1-meth- 2 hydroxymphthalene 3 carboxylic acid 4 Yellowish Bordeaux.

oxy-benzene. chloro -z-anisidide. No. 12 4-to1uene suifonmethylamino-2-amino-1-meth- 2 hydroxynaphthelene 3 carboxylic acid a Bordeaux.

- oxy-benzene. naphthylamide. N o. 13 4-toluene sulfonmethylamino-2-amino-l-meth- 2 hydroxynaphthalene 8 carboxylic acid B Yeliowish Bordeaux. oxynzene. naphthylamide. No. 14 4-toiuene-sultonbenzylamino-2-amino-l-meth- 2 -hydroxynaphthalene -3 carboxylio a c i d 6 Bluish-red.

oxly-benzene. chloro-2-toluidide. No. 15 d-to uene-sulfonbenzylamino-B-emino-l-meth- 2 hydroxynaphthalene 3 carboxylic acid B Yeilowish Bordeaux.

oxy-benzene. naphthylamide.

In our 00- ending application Serial No. wherein Z represents alkyl or aralkyl and R 15,121, filed arch 12, 1925, slmllar azo dyeand R represent aryl radlcles. stufis are described. 2. As new compounds, the azo dyestufis of 80 We clalmz the general formula:

1. As new compounds, the azo dyestufis of 081m the general formula:

N-N o-ukyi -Z O-N-R N-Z oo-N-n 1 wherein Z represents alkyl or aralkyl and R and R represent aromatic nuclei of the group including the benzene and naphthalene series. 3. As new compounds, the azo dyestufls of the general formula:

which dyes cotton yarn a bright claret-red tint with a hue of good fastness.

5. The process which comprises diazotizing a compound of the general formula:

N==N Q-alkyl on NH] N-OH:

1 N4 40 wherein R and R represent aromatic nuclei of the group including the benzene and naph- 1 thalene series.

4. As a new. product, the azo dyestufis of wherein Z represents alkyl or aralkyl and R the probable formula: an aryl radicle and coupling the diazo 00111- 0cm pound thus obtained with a 2 hydroxynaphthalene-3-carboxylic acid-arylamide. N==N In testimony whereof, we affix our signatures. 0H CH3 HERMANN WAGNER. 01 3 N OTTO soHsT. 

